Oxazolidinedione derivatives, method of producing the derivative

Details Oxazolidinedione derivatives, method of producing the derivative Oxazolidinedione derivatives, method of producing the derivative

1987-06-11

1989-04-04

Daus, Donald G.

Chemistry: fertilizers

Processes and products

Forms or conditioning

548226, A01N 4376, C07D26306

Patent

active

048182729

DESCRIPTION:

BRIEF SUMMARY
DETAILED DESCRIPTION OF THE INVENTION



Field of the Invention

The present invention relates to oxazolidinedione derivatives and a production method thereof, and particularly to oxazolidinedione derivatives expressed by the following formula: ##STR2## (wherein R.sup.1, R.sup.2 and R.sup.3 independently denote hydrogen atoms, halogen atoms, nitro groups, alkyl groups, alkoxyl groups, alkenyloxy groups, alkynyloxy groups or cycloalkyloxy groups; R.sup.4 and R.sup.5 independently denote hydrogen atoms, alkyl groups or aryl groups or may be combined with each other to form a polymethylene chain; and the above-described alkyl groups, alkoxyl groups, alkenyloxy groups, alkynyloxy groups, cycloalkyloxy groups and aryl groups may be substituted), a production method thereof and herbicides containing the derivatives as an active ingredient.
Various derivatives having substituents at the 5-positions of oxazolidinedione rings have been known, but oxazolidinedione derivatives having methylidene groups at the 5-positions have not been reported at all because of difficulty in the synthesis thereof.
In addition, although many heterocyclic compounds having a weed-killing activity have previously been synthesized and put to practical use, no practical oxazolidinedione derivative having weed-killing activity has previously been known.


Problems to be Solved by the Invention

It is an object of the present invention to provide novel compounds having high selectivity for weeds and powerful weed-killing activity and to provide an industrial method of producing compounds and herbicides containing these compounds as an active ingredient.


Means for Solving the Problems

The inventors have found that vigorous weed-killing activity and high selectivity for various weeds may be imparted to herbicides by introducing methylidene groups having various substituents at the 5-positions of oxazolidinedione derivatives.
The target compounds of the present invention are shown by the formula (I), wherein R.sup.1, R.sup.2 and R.sup.3 independently denote hydrogen atoms; nitro groups; halogen atoms such as fluorine, chlorine, bromine and iodine atoms; straight or branched chain alkyl groups having 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups which may be substituted by one or more halogen atoms; alkoxy groups having 1 to 18 carbon atoms, preferably 1 to 8 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, t-butoxy, groups which may be substituted by one or more alkoxycarbonyl groups (2 to 18 carbon atoms) or halogen atoms; cycloalkoxy groups having 3 to 12 carbon atoms, preferably 3 to 8 carbon atoms, such as cyclohexyloxy, cyclopentyloxy, and cyclopropyloxy groups which may be substituted by one or more lower alkyl groups (1 to 5 carbon atoms) or halogen atoms; straight or branched chain alkenyloxy groups having 2 to 12 carbon atoms, preferably 2 to 8 carbon atoms, such as allyloxy, methallyloxy, propenyloxy, butenyloxy, pentenyloxy and hexenyloxy groups which may be substituted by one or more halogen atoms; or straight or branched chain alkynyloxy groups having 2 to 12 carbon atoms, preferably 2 to 8 carbon atoms, such as propargyloxy, 1-methylpropargyloxy, 1,1-dimethylpropargyloxy, 2-butynyloxy, 3-butynyloxy, 2-pentynyloxy, 3-pentynyloxy groups which may be substituted by one or more halogen atoms; and R.sup.4 and R.sup.5 independently denote hydrogen atoms, straight or branched chain alkyl groups having 1 to 18 carbon atoms, preferably 1 to 8 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, and n-octyl which may be substituted by one or more halogen atoms; aryl groups having 6 to 10 carbon atoms such as phenyl, p-chlorophenyl, p-fluorophenyl, m, p-dimethoxyphenyl, and p-methylphenyl which may be substituted by halogen atoms or lower alkyl groups having 1 to 3 carbon atoms; or R.sup.4 and R.sup.5 may be combined with each other to form a straight or branched chain polymeth

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